1. Field of the Invention
This invention relates generally to the field of novel organic chemical compounds useful generally as surfactants and more particularly certain species useful as surface active agents for detergent preparation and catalysts for the preparation of isocyanurate foams.
2. Description of the Prior Art
Ethoxylated alcohols and alkyl phenols are well known for their use as non-ionic surface active agents with the hydroxyethoxy groups providing the hydrophilic portion of the molecule. The manufacture of these materials is well well known from the patent literature by the reaction of ethylene oxide with aliphatic alcohols or the phenolic hydroxyl group of an alkyl phenol. If propylene oxide is substituted for any, or all, of the ethylene oxide, then the compound becomes less water soluble and more oil soluble.
Hydroxyl terminated compounds may be converted into primary amines by several methods. One such method is to prepare an amine from a hydroxyl terminated polyoxyalkylene aliphatic compound is through the reductive amination of the hydroxyl group by reacting ammonia with the hydroxyl terminated compound, usually in the presence of hydrogen, and a catalyst. While a number of catalysts are well known, the catalyst described in U.S. Pat. No. 3,152,998, for example, and the method described in U.S. Pat. Nos. 3,644,370 and 3,390,184 particularly describe this preparation of primary amines.
Another method for the preparation of such primary amines is to react the hydroxyl containing compound with alkenyl nitriles, such as acrylonitrile in the presence of gaseous ammonia to form a 3-alkoxypropiononitrile as described, for example, in U.K. Pat. No. 869,405. The nitrile group is then catalytically reduced, in the presence of hydrogen, to form the primary amine compound.
The acrylonitrile reaction can be employed either directly to the aliphatic alcohol or to the hydroxyl group of an alkoxylated alcohol or alkyl phenol.
Certain of these compounds are useful in the preparation of the compounds of this invention through the reaction of the primary amino group with various other compounds which provide the overall molecule with reactive groups for improved water solubility. Thus, the oil solubility of prior art surface active compounds can be improved by the addition of propylene oxide to the aliphatic alcohol or alkyl phenol; and the water solubility improved by the conversion of the compound of this invention to the salts of the light metals of Group 1a or 2a on the Periodic Chart, particularly the sodium and potassium salts of the compounds of this invention. Surprisingly, it has been discovered that these compounds do not possess the prior art detriment of being precipitated by the presence of calcium ions from calcium salts in the water. The presence of calcium ions in the water have been found to be the downfall of many prior art surface active agents.
The primary amino terminated compounds used as the precursor of this invention are reacted with dibasic acids, most particularly their anhydrides, and other compounds to form the compounds of this invention. While the reactions of a number of the substituents added to prepare the compounds of this invention with primary amines is well documented in the prior art; none of the prior art recognizes the reaction of these compounds with the precursors used to form the novel compounds of this invention. For example, U.S. Pat. No. 2,757,125 teaches the reaction of itaconic acid with dodecyl amine. While the sodium salt of this material, a white powder, had good foaming properties in an aqueous solution, the calcium salt was insoluble in water. It will be shown that the compounds of this invention do not suffer from such an infirmity.
Further, other itaconic acid and amine reaction products have been found to be anticorrosive agents for metals and lube oil additives, as described in U.S. Pat. Nos. 3,224,968 and 3,224,975. Again, the reaction was with a straight chain alkyl amine or fatty acid amine. The reaction of tetrapropenylsuccinic anhydride with an amine such as triphenyl amine has been described as useful in preparing a lubricating oil additive in German Offfen. No. 2,447,550; the epoxidation of a 2-alkyl amine is described in German Offen. No. 2,429,791 for the formation of corrosion inhibiting amine emulsions; and other corrosion inhibiting compounds are described in U.S. Pat. No. 2,604,451 wherein the reaction of an amine is with an alpha-substituted dicarboxylic acid or acid anhydride such as alkenylsuccinic acids and phenoxyphenylalkylsuccinic acids is described.
Still, another copious prior art describing related reactions and related problems is available, the solution discovered by applicants has not manifested itself. This is particularly true with respect to the calcium salt solubility and the discovery that pyrrolidinone compounds of this invention, when existing as the Group 1a and 2a metal salts, are outstanding catalysts for the production of isocyanurate foams as will be more particularly described herein.